Race You to the City
by ArtsyMew
Summary: After meeting up near Castelia, May and Drew decide to explore the big city together. Contestshipping
1. Race You to the City

_A/N: It's been about…5 years since I wrote the prequel to this idea? Welp, better late than never. Enjoy!_

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"Race you to the city!"

A warm breeze hits them while riding their bikes across the highway bridge, cars on their way to early morning shifts bustling beneath them. The last remainders of nightfall shadow the Castelia skyline.

"Most restaurants aren't even open yet, May."

"I never said I was hungry!" Her stomach protests. Drew stifles a laugh.

She unexpectedly met up with her rival during one of her expeditions through Pinwheel Forest yesterday. Also heading to Castelia City for the upcoming contest, he suggested they go together. After camping the night out, they woke up before dawn to cross the Castelia Bridge and explore the city before it became its infamous lively self.

"We'll get some food once we get there. There's probably a hundred Sawsbucks waiting for our hard-earned money."

Surprised he directed his wit _not_ at her for once, May smiles at the prospect of yummy overpriced café food and a nice frap-

"Try swallowing some Cutieflies until then."

Ah. There it is.

She grimaces at the mental image and turns, preparing a retort, but Drew isn't beside her. Looking behind, she notices he stopped, gazing intently at the horizon. Stopping her bike, May turns her head in the same direction.

She isn't a morning person; Drew practically dragged her to the bridge this morning. Yet, experiencing how the sun as it peaks out from the sea, bathing the city in a warm light that reflects off the buildings in front of them, makes her want to set her alarms this early more often.

The coordinators admire the spectacle, undisturbed by the muffled road rage and cruise engines. May closes her eyes and takes a deep breath, tasting a twinge of salt in the air. It reminds her of Hoenn.

She voices her nostalgia. Drew laughs.

"Yeah, reminds me of your Beautifly's Morning Sun," he stretches his arms, breathing in the air. "Feels like I got restored by it, too."

Drew flattered her Pokémon and her skills many times before, but she's never gotten used to it. If he notices her blush, he doesn't comment.

"Oh! I got an idea. Beautifly, take the stage!"

Drew looks at her quizzically before understanding, calling out his Roserade. Both Pokémon emerge, questioning their trainers for sending them out before noticing the sunrise. Without need of further prompting, they perform their restorative moves.

As their Pokémon restore their energy, the coordinators re-mount their bikes and continue towards Castelia. Beautifly happily chirps as it flies over them, wings sparkling. Meanwhile, Drew hides his initial struggle with Roserade's added weight on his bike but adjusts quickly, managing to pass May on the narrow road.

"I thought you didn't wanna race?"

He doesn't even have to turn around for her to _know_ he's smirking. "It's not a race if the winner's decided."

Oh, _now_ she's irked. She peddles vigorously, motivated by the sweet, sweet victory she will shove in Drew's smug face. Drew peddles a little faster, not willing to let May pass him. Roserade grips the sides of the basket in panic, sending her trainer a glare that he ignores. He's not about to admit he's having a little fun. Despite always teasing her childishness, May does bring him out of his cautious shell.

Well, maybe cautiousness _is_ better in some situations; especially when you're carrying a 35-pound, nearly meter tall Pokémon while biking up concrete.

He doesn't hear May shouting at him to watch out through his adrenaline rush. Next thing he's on the ground, a little disoriented. His bike fell beside him, its wheels still spinning. Roserade jumped out as they fell, landing gracefully near her trainer.

"Arceus, Drew. Are you OK?" May gets off her bike and crouches beside him, Beautifly hovering above. "You're hurt!"

Pushing himself up with scraped hands, he notices his pant leg torn up, revealing an ugly cut on his knee. It doesn't look too deep nor does it hurt much when he bends his leg. Then again, the remaining adrenaline probably clouds his judgement.

"Shame, I liked these pants."

"It's not funny!"

He flicks his messed-up hair, attempting to regain some finesse. His hair looks worse. The feeble attempt makes her laugh though, and he supresses a smile. This clumsy situation is unlike him. Roserade also giggles at her trainer's expense. Drew deadpans at her, but internally releases a breath knowing his Pokémon is unharmed.

"May, I'm fine," he tries standing up, wincing as a sharp sting registers as his weight falls on his knees. "I'll get it checked once we get to the Centre. Let's go."

May's not having it though. She exchanges a look with Roserade, who looks just as equally fed up as she is worried for her trainer. Seriously, why are men so stubborn?

"Wait a sec, Drew," she calls Beautifly, who perches itself on her head. Drew's about to dismiss May because really, he doesn't want her worrying, but Roserade gives him a pointed look and he obliges.

May instructs her Beautifly to use Morning Sun again. Roserade gets the gist, using Synthesis near her trainer's leg. A few minutes later, the cut on his leg is nothing more than a faded scar. His hands also healed up. He clenches and opens them up a couple times, staring at them and his leg in awe.

"Huh, looks like I _did_ get restored by it," he stands up easier now, mind clear. "Thank you, Roserade and Beautifly."

"Hey, I helped too!"

"I didn't know you could do Morning Sun, May," Drew dusts himself off, running a hand through his hair as she stands up. She's starting to regret helping him. "But seriously, thank you."

The genuine sincerity he looks at her with takes her back. Despite his smug attitude and sarcastic comments, she understands why so many fangirls admire him – herself included.

"I-its no problem," she turns away, flustered he's made her feel like this _twice_ already in the span of what, ten minutes? She feels silly for always wearing her heart on her sleeve. "I'm glad you're better. Let's get going!"

Thanking their Pokémon once more, the coordinators call them back into their Pokeballs. The sun rose a bit higher in the short amount of time, further basking the city in a livelier light. Steady lines of traffic continue forming below them. Drew suggests they walk the remainder of the way. May agrees, not questioning his reasoning. He internally thanks her for it.


	2. Please buy some new pants

_A/N: I just want him to get rid of those pants. For everyone's sake._

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"You need new pants."

Drew finishes his espresso, throwing the Sawsbucks cup in a nearby bin. May hungrily takes another bite of her bagel, staring unsatisfyingly at Drew's pants.

"I suppose you're right," Drew picks at the frays lining the tear, frowning. "These were my favorite."

May's cringe goes by unnoticed at his statement. He's handsome; anyone with a pair of working eyes can tell. His elegant and suave contest persona make him a popular coordinator. He's always a step ahead of her. She sometimes finds these qualities unfair, but looking at those pants…

Arceus must have decided to be fair; he gave Drew a terrible sense of style.

"Let's go shopping!" she insists, "we got here early, and we were just looking around today."

"Wait, we?"

"Yeah! What else am I supposed to do while waiting for you?"

"Practice your appeals?" he answers as if it's obvious. May sighs, he has a point. She _should _practice with Glaceon given that the warmer weather affects ice-type attacks…but…

She glances at those _pants_ again. Their color reminiscent of her first impression of Drew all those years ago: obnoxious. She never cared much before, dismissing them as an odd Larousse fashion. But all those same years of getting to know him – growing closer - made those once-tolerable pants increasingly noticeable.

As her friend Dawn would likely say: not helping someone in need of fashion advice is a disservice.

Arceus knows he needs it.

"Our Pokémon just healed up," she reasons, "I'd rather give them more time to rest before practicing. Plus, I already planned to shop a little later anyways!"

Drew prepares another excuse, but seeing May beaming up at him excitedly doesn't exactly help in his favor. A few more seconds pass but the fiery determination shining in her big, blue eyes doesn't dim. Honestly, he should have expected this.

He sighs, defeated.

"I guess having you as a second opinion wouldn't be the worst that's happened to me today."

* * *

Drew's a simple guy when it comes to clothes: he finds something practical; he wears it. It's simplicity he engages in outside of coordinating, preferring to leave the showing-off to his Pokémon. He's worn these pants since the beginning of his journey and they've lasted, needing to only roll up the cuffs during his growth spurt. He also doesn't mind their color, thinking it quite nice. Though, he knew he would have to change them eventually.

Just not to the khaki pants May's showing him.

"Drew! This shade goes well with your hair color!" she lifts them closer to him eagerly, then another glimmer catches her eye, "oh! those red ones would look great too!"

"Sure, the red ones are nice," he shrugs as May beams, "if I wanted to look like a Christmas tree."

Drew stifles a laugh when face morphs into a frown and she huffs away to another rack. It's the fifth store they've gone into. _Fifth_. He found something at the first one yet May _insisted_ they compare other options. She could probably go on for hours and its already nearing noon. He knew he was going to regret this. Why did he let her come along again?

She's currently holding a pair of navy-blue pants and staring intently at Drew's hair when she catches his gaze. She smiles sheepishly, a light blush dusting her cheeks. His heart flutters.

Ah. That's why. Stupid feelings.

Still, as much as he enjoys spending time with her, his general disinterest for shopping and his exposed knee-cap urge him to wrap this up.

May practically skips to meet him, another pair of pants in hand. "Any luck finding something?"

Time to be honest with her.

"Look May, I appreciate your help, but I'll just look for something later."

He immediately feels like an ass when her expression falls.

"Oh…" she clutches the pants, "I'm sorry Drew. Guess I got carried away. You don't like doing this kinda stuff, do you?" She tries smiling at him. "I'll wait while you look for some- "

"Actually," he interrupts a little desperately, gesturing at the pair she's holding, "those ones aren't bad."

Drew honestly hadn't paid much attention to the ones she'd been holding. So, here he was in the dressing room much to May's excitement and his dismay. Unlike his pants, these were plain, black cargos. An interesting choice considering her attempts so far to try out "fashionable" statements. Though not something he saw himself picking out, they're surprisingly comfortable and fit him well. He tucks in the violet shirt he _did_ pick out (that looks very similar to the one he already owns) and exits the stall.

May's waiting on the bench nearby. She smiles wide when she sees him, rushing up to him.

"Drew!" she gasps, clasping her hands together. Her smile turns a bit smug, "I knew these would suit you!"

Drew's too taken aback at her enthusiastic response to remark. Contest-Drew would typically brush it off with a flick of his hair and a confident attitude. Normal-Drew, on the other hand, doesn't know how to handle compliments from May, his rival and the girl he's been hopelessly in love with for years.

So, he just stands there, eyes wide and blushing and willing himself to snap out of it. Meanwhile, May's too focused on inspecting his outfit to notice. Her eyes narrow. "Wait, your shirt looks a bit off…"

She steps forward, reaching to undo the top button of his shirt and Drew (if even possible) turns a darker shade of red. She's _too_ close. Close enough to view how impossibly _blue_ her eyes are through long lashes. Close enough to feel her breath tickle his neck as she fixes his collar. Close enough to smell the sweet perfume she tried on at one of the stores. Close enough to hear her heart beat over his own booming thrum while she gently loosens the tuck on his shirt.

Close enough that, if she allowed him, he could find out the taste of her lips.

"There…" she admires her work, oblivious to the flustered mess she's rendered her rival in. It's only when she looks up and notices how _red_ he is – how _lovely_ flecks of jade appear up close in his gorgeous forest eyes - that she realizes what she's doing.

_Now_ she's blushing.

"I-I'm so sorry!" she jumps away, arms flailing. "I didn't mean- I j-just wanted to fix the button and then saw how the collar was a bit wrinkled and—and-"

Seeing how she's out-flustering him, Drew clears his throat to regain his composure. "Don't worry, I know its hard for you to keep your hands off me."

She stops rambling and glares at him, cheeks puffing out in annoyance. He finds it both amusing and adorable thinking how she resembles a Cherubi. "You're so full of it."

"If by 'it' you mean good lucks and a sharp wit, then you're absolutely right, May". He flicks his hair, mostly because he knows doing so will further infuriate her. He holds in a chuckle when it does.

"Well, what do _you_ think of them?"

Right, he had yet to opinion on these pants. Pondering, he tugs at the rough fabric, sliding his hands in their large pockets (another plus) before answering. "I didn't have high expectations," he smirks when May pouts, "_but_ they're comfortable. If they have you practically swooning, they probably don't look bad either."

"Hey! I'm just glad you like _something_ I picked out," she crosses her arms defensively. Then she's looking at her shoes, attempting to hide another blush. "And you _do_ look really good, so…"

He's convinced.

After paying for the clothes at the register, Drew wears them out the store. May's gloating in her success, but he figures he'll let her be for now. Instead, he holds his old pants in front of him, looking wistful. "Shame I have to part with these though," May turns to him curiously, "maybe I could turn them into shorts."

"Please don't."


	3. Casteliacone

_A/N: May's hungry for ice cream._

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Standing under the noon sun, May curses falling for a tourist trap while waiting in the long, long line up for a single, overpriced Casteliacone.

"Come on, Drew!" She had insisted, willing to make the most of it despite his skepticism, "we gotta try it since we're here!"

Half an hour later and ice cream in hand, the coordinators walk further up the street until they reach a small park with a flowing fountain in its center. They sit at a bench beneath a tree that offers a welcome shade from the heat. Drew chuckles as May gives a passing family a thumbs up when she spots the Casteliacones in their hands.

"That hungry, huh?" He notes the lack of ice cream left on her cone.

"It was a small cone!"

A couple of minutes pass by in silence, something rare for the two of them. Usually they would find something to talk about, like coordinating strategies or upcoming contests - or just bicker. But the park, the nice shade and the decent ice cream provide a comfortable atmosphere that neither feel the need to break just yet. May's surprised Drew hasn't poked more fun at her either.

Curious, May glances at said coordinator while taking a bite off her cone. He's looking at the group of break dancers practicing near the fountain, seemingly lost in thought. He's still working on the ice cream part, and May wants to tease that he's a slow eater. But a drop of cream dribbling past his lip catches her attention. She watches as his eyes narrow in annoyance before his tongue skims the drop in one slow, smooth motion before going to lick the ice cream again. And again. And again. A few drops almost fall on his fingers, but his tongue is quick to catch them.

She can't seem to look away, feeling pulled in further with each lick. She starts feeling very, very hot for some reason. An odd thought of wanting to be the ice cream crosses her mind. She dismisses it. Another thought of Drew licking the ice cream off of her- Arceus. Did the heat really affect her that much? So much for being from Hoenn.

Eventually Drew senses her staring and turns to look at her. She gulps as his Adam's apple bobs up when he swallows.

"Still hungry?" he teases.

"Uh-huh"

Drew stares are her quizzically before his eyes widen. Suddenly he leans forward to graze her cheek with his hand, freezing May in place. Her heart thrums. His thumb gently swipes her lip and she instinctively shuts her eyes...

"You do want the rest of my cone, don't you? I'm quite full anyway."

Huh?

Opening her eyes, she sees Drew back on his side of the bench, looking at her amusingly. His hand outstretches his remaining Casteliacone in offering. She feels confused and surprisingly frustrated. Wasn't he about to-

"By the way, you should slow down, May," Drew remarks with a flip of his hair, "I can't keep cleaning crumbs off your face."

She snatches the Casteliacone from him and takes a huge bite of it, crunching loudly while uttering a muffled "thanks". She throws crumbs at him when he chastises about speaking with her mouth full.

Curse the heat.


	4. Mini update!

_Update!_

Hello fellow Contestshippers!

I hope you are staying well and safe during these times. Currently working on a new chapter update for this story! I haven't forgotten about it 😊 Right now I'm juggling an online semester at university, but I will continue this story as it gives me joy and escapism from the aforementioned uni lol. The main reason I had not updated since last Fall was because the past spring semester was my first full term back at university after taking a couple semesters to gain work experience.

Anyway, just a mini update. The upcoming chapter will take place in Castelia's Café Sonata during a suddenly rainy afternoon…

~ArtsyMew


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